1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (2E)-3-{6-[(1-benzyl-3-pyrrolidinyl)amino]-3-pyridyl)-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide

Participants

Reaction Steps

A mixture of (2E)-3-{6-[(1-benzyl-3-pyrrolidinyl)amino]-3-pyridyl}acrylic acid (400 mg), O-(tetrahydro-2H-pyran-2-yl)hydroxylamine (159 mg), HOBt (175 mg) and EDCI (202 mg) in DMF (10 ml) was stirred at ambient temperature for 15 hours. The reaction mixture was poured into a mixture of AcOEt-H2O and the organic layer was washed with brine and dried over MgSO4. The solvent was evaporated in vacuo and the residue was chromatographed on silicagel eluting with AcOEt-MeOH (9:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to give (2E)-3-{6-[(1-benzyl-3-pyrrolidinyl)amino]-3-pyridyl)-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide (170 mg)

Provenance & Evidence